Organic light emitting diode

ABSTRACT

The present specification relates to an organic light emitting diode.

This application is a National Stage Application of InternationalApplication No. PCT/KR2014/009895, filed Oct. 21, 2014, and claims thebenefit of Korean Application No. 10-2014-0120941, filed Sep. 12, 2014,all of which are hereby incorporated by reference in their entirety forall purposes as if fully set forth herein.

TECHNICAL FIELD

This application claims priority to and the benefit of Korean PatentApplication No. 10-2014-0120941 filed in the Korean IntellectualProperty Office on Sep. 12, 2014, the entire contents of which areincorporated herein by reference.

The present specification relates to an organic light emitting diode.

BACKGROUND ART

An organic light emission phenomenon is an example of converting currentinto visible rays by an internal process of a specific organic molecule.A principle of the organic light emission phenomenon is as follows.

When an organic material layer is positioned between an anode and acathode, if a voltage is applied between two electrodes, electrons andholes are respectively injected from the cathode and the anode into theorganic material layer. The electrons and the holes which are injectedinto the organic material layer are recombined to form excitons, andlight is emitted while the excitons fall down to a bottom state again.In general, an organic light emitting diode using this principle may beconstituted by a cathode, an anode, and an organic material layerpositioned therebetween, for example, an organic material layerincluding a hole injection layer, a hole transport layer, a lightemitting layer, and an electron transport layer.

A material used for the organic light emitting diode is mostly a pureorganic material or a complex compound where an organic material andmetal form a complex, and may be classified into a hole injectionmaterial, a hole transport material, a light emitting material, anelectron transport material, an electron injection material, and thelike according to the purpose thereof. Herein, an organic materialhaving a p-type property, that is, an organic material that is easilyoxidized and has an electrochemically stable state during oxidation, ismostly used as the hole injection material or the hole transportmaterial. Meanwhile, an organic material having an n-type property, thatis, an organic material that is easily reduced and has anelectrochemically stable state during reduction, is mostly used as theelectron injection material or the electron transport material. As alight emitting layer material, a material having both p-type and n-typeproperties, that is, a material having a stable form in both oxidationand reduction states is preferable. Also, a material having high lightemitting efficiency for converting the exciton into light when theexciton is formed is preferable.

In the art, there is a demand for developing an organic light emittingdiode having high efficiency.

PRIOR ART DOCUMENT Non-Patent Document

-   Applied Physics Letters 51, p. 913, 1987

DETAILED DESCRIPTION OF THE INVENTION Technical Problem

The present specification has been made in an effort to provide anorganic light emitting diode having high light emitting efficiency.

Technical Solution

An exemplary embodiment of the present specification provides an organiclight emitting diode including: an anode; a cathode; a light emittinglayer provided between the anode and the cathode; an organic materiallayer including a compound represented by the following Chemical Formula1 and provided between the cathode and the light emitting layer; and anorganic material layer including a compound represented by the followingChemical Formula 2 and provided between the anode and the light emittinglayer.

In Chemical Formula 1,

X1 to X3 are the same as or different from each other, and are eachindependently N or CH,

at least one of X1 to X3 is N,

Cy1 and Cy2 are the same as or different from each other, and are eachindependently a substituted or unsubstituted monocyclic or polycyclicaromatic cycle having 6 to 30 carbon atoms; or a substituted orunsubstituted monocyclic or polycyclic heterocycle having 2 to 30 carbonatoms,

L1 is a substituted or unsubstituted monocyclic or polycyclic arylenegroup having 6 to 30 carbon atoms,

m is an integer of 1 to 4,

in the case where m is 2 or more, L1s are the same as or different fromeach other, and

Ar1 and Ar2 are the same as or different from each other, and are eachindependently a substituted or unsubstituted monocyclic or polycyclicaryl group having 6 to 30 carbon atoms; or a substituted orunsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30carbon atoms, and

in Chemical Formula 2,

Ar3 and Ar4 are the same as or different from each other, and arehydrogen; deuterium; a substituted or unsubstituted monocyclic orpolycyclic aryl group having 6 to 30 carbon atoms; or a substituted orunsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30carbon atoms,

L2 is a substituted or unsubstituted monocyclic or polycyclic arylenegroup having 6 to 30 carbon atoms,

n is an integer of 0 to 5,

in the case where n is 2 or more, two or more L2s are the same as ordifferent from each other,

R1 to R7 are the same as or different from each other, and are eachindependently hydrogen; deuterium; a substituted or unsubstitutedstraight-chained or branch-chained alkyl group having 1 to 30 carbonatoms; a substituted or unsubstituted monocyclic or polycyclic arylgroup having 6 to 30 carbon atoms; or a substituted or unsubstitutedmonocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms,or adjacent groups are bonded to each other to form a substituted orunsubstituted aromatic cycle, and

Y1 and Y2 are the same as or different from each other, and are eachindependently hydrogen; deuterium; a substituted or unsubstitutedstraight-chained or branch-chained alkyl group having 1 to 30 carbonatoms; a substituted or unsubstituted monocyclic or polycyclic arylgroup having 6 to 30 carbon atoms; or a substituted or unsubstitutedmonocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms,or Y1 and Y2 are bonded to each other to form a substituted orunsubstituted aromatic cycle.

Advantageous Effects

An organic light emitting diode according to an exemplary embodiment ofthe present specification provides a low driving voltage and/or highefficiency.

BRIEF DESCRIPTION OF DRAWINGS

FIG. 1 illustrates an example of an organic light emitting diodeaccording to an exemplary embodiment of the present specification.

FIG. 2 illustrates an example of an organic light emitting diodeaccording to an exemplary embodiment of the present specification.

EXPLANATION OF REFERENCE NUMERALS AND SYMBOLS

-   -   101: Substrate    -   201: Anode    -   301: Hole transport    -   401: Electron blocking layer    -   501: Light emitting layer    -   601: Electron transport layer    -   701: Cathode    -   801: Electron injection layer

BEST MODE

Hereinafter, the present specification will be described in more detail.

In the present specification, unless explicitly described to thecontrary, the word “comprise” and variations such as “comprises” or“comprising”, will be understood to imply the inclusion of statedelements but not the exclusion of any other elements.

In the present specification, it will be understood that when an elementis referred to as being positioned “on” another element, it can bedirectly on the other element or intervening elements may also bepresent between the two elements.

An organic light emitting diode according to an exemplary embodiment ofthe present specification includes both an organic material layerincluding a compound represented by Chemical Formula 1 and an organicmaterial layer including a compound represented by Chemical Formula 2.

According to the exemplary embodiment of the present specification, theorganic material layer including the compound represented by ChemicalFormula 1 is an electron transport layer, an electron injection layer,or a layer simultaneously transporting and injecting electrons.

According to one exemplary embodiment of the present specification, theorganic material layer including the compound represented by ChemicalFormula 1 is the electron transport layer.

According to another exemplary embodiment of the present specification,an organic material layer including a compound represented by ChemicalFormula 1 is an electron injection and electron transport layer.Specifically, in the organic light emitting diode according to theexemplary embodiment of the present specification, in the case where theelectron injection layer is not provided, the organic material layerincluding the compound represented by Chemical Formula 1 may serve asboth the electron injection layer and electron transport layer.

Further, according to another exemplary embodiment of the presentspecification, the organic light emitting diode may include only theorganic material layer including the compound represented by ChemicalFormula 1 between a cathode and a light emitting layer. In anotherexemplary embodiment, the organic light emitting diode may furtherinclude an additional organic material layer between the cathode and theorganic material layer including the compound represented by ChemicalFormula 1; or between the light emitting layer and the organic materiallayer including the compound represented by Chemical Formula 1.

According to the exemplary embodiment of the present specification, theorganic material layer including the compound represented by ChemicalFormula 2 is a hole transport layer.

In the related art, an organic material having an n-type property, thatis, an organic material that is easily reduced and has anelectrochemically stable state during reduction, is mostly used as anelectron transport material. However, the organic material iselectrochemically unstable during oxidation, a novel electron transportmaterial has been continuously studied.

The compound represented by Chemical Formula 1 according to theexemplary embodiment of the present specification has a bipoar typehaving both a p-type property (cycle group including Cy1 and Cy2) and ann-type property (cycle group including X1 to X3), and thus has a stablestate in both oxidation and reduction states. Accordingly, an effectthat when an exciton is formed, light emitting efficiency of convertingthe exciton into light is high may be obtained.

Like the organic light emitting diode according to the exemplaryembodiment of the present specification, in the case where the compoundboth having the bipoar property of the p-type and n-type properties andrepresented by Chemical Formula 1 is used as the electron transportlayer and the organic material layer including the compound representedby Chemical Formula 2 is used as the hole transport layer, an increasein efficiency may be maximized.

In the exemplary embodiment of the present specification, hole mobilityof the compound represented by Chemical Formula 2 is 5×10⁻⁶ cm²/Vs ormore. In another exemplary embodiment, hole mobility of the compoundrepresented by Chemical Formula 2 is 5×10⁻⁶ cm²/Vs or more under anelectric field condition of 0.1 MV/cm. In another exemplary embodiment,hole mobility of the compound represented by Chemical Formula 2 is 10⁻⁶cm²/Vs or more.

Hole mobility of the compound represented by Chemical Formula 2according to the exemplary embodiment of the present specification is5×10⁻⁶ cm²/Vs or more under the electric field condition of 0.1 MV/cm,and is higher than that of an existing hole transport material.Accordingly, by increasing the number of excitons generated in the lightemitting layer, high efficiency may be expected but leakage of holes tothe cathode may be caused. However, in the case where the organicmaterial layer including a heterocyclic compound represented by ChemicalFormula 1 according to the exemplary embodiment of the presentspecification is provided between the light emitting layer and thecathode, since the compound represented by Chemical Formula 1 is thebipolar type including both the p type and the n type rather than thepure n type, the generated exciton as well as the holes leaked byChemical Formula 2 may be effectively confined in the light emittinglayer, and a stable form of the exciton, that is, hole-electron pairsagainst chemical attack may be maintained, a life-span as well asefficiency may be maximized.

In the present specification, hole mobility may be measured by a methodused in the art. Specifically, a time of flight (TOF) method or a spacecharge limited current (SCLC) measurement method may be used, and themethod is not limited thereto. In the present specification, in order tomeasure the space charge limited current (SCLC), a film thickness of thematerial may be set to 1000 nm or more, and thus hole mobility may bemeasured.

In the exemplary embodiment of the present specification, hole mobilityof the compound represented by Chemical Formula 2, which is measured bythe time of flight (TOF) method, is 5×10⁻⁶ cm²/Vs or more.

In one exemplary embodiment of the present specification, afterhexanitrile hexaazatrilephenylene is heated under the vacuum on an ITOsubstrate to be deposited in a thickness of 5 nm, a hole transportmaterial represented by Chemical Formula 2 is deposited in a thicknessof 200 nm, and aluminum is the deposited in a thickness of 100 nm ormore to manufacture a sample. A current density (mA/cm²) to a voltage ofthe sample may be measured to calculate hole mobility in a space chargelimited current (SCLC) region.

According to the exemplary embodiment of the present specification, theorganic light emitting diode further includes one or two or more layersfrom the group consisting of the electron injection layer and theelectron transport layer between the light emitting layer and thecathode.

According to another exemplary embodiment of the present specification,the organic material layer including the compound represented byChemical Formula 1 is the electron transport layer, and further includesthe electron injection layer provided between the electron transportlayer and the cathode.

According to the exemplary embodiment of the present specification, theorganic light emitting diode further includes one or two or more fromthe group consisting of a hole injection layer, a hole transport layer,and an electron blocking layer between a light emitting layer and ananode.

According to another exemplary embodiment of the present specification,the organic material layer including the compound represented byChemical Formula 2 is the hole transport layer, and further includes theelectron blocking layer provided between the hole transport layer andthe light emitting layer.

According to the exemplary embodiment of the present specification, theelectron blocking layer is provided to come into contact with the lightemitting layer.

In the present specification, examples of substituent groups will bedescribed below, but are not limited thereto.

The term “substituted” means that a hydrogen atom bonded to a carbonatom of a compound is changed into another substituent group, asubstitution position is not limited as long as the substitutionposition is a position at which the hydrogen atom is substituted, thatis, a position at which the substituent group can be substituted, and inthe case where two or more atoms are substituted, two or moresubstituent groups may be the same as or different from each other.

In the present specification, the term “substituted or unsubstituted”means that substitution is performed by one or two or more substituentgroups selected from the group consisting of deuterium; a halogen group;a nitrile group; a nitro group; an imide group; an amide group; ahydroxy group; a substituted or unsubstituted alkyl group; a substitutedor unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxygroup; a substituted or unsubstituted alkenyl group; a substituted orunsubstituted amine group; a substituted or unsubstituted aryl group;and a substituted or unsubstituted heterocyclic group, substitution isperformed by a substituent group where two or more substituent groups ofthe exemplified substituent groups are connected, or there is nosubstituent group. For example, the “substituent group where two or moresubstituent groups are connected” may be a biphenyl group. That is, thebiphenyl group may be an aryl group, or may be interpreted as asubstituent group where two phenyl groups are connected. The term“substituted or unsubstituted” means that substitution is performed bythe substituent group where two or more substituent groups of theexemplified substituent groups are connected or there is nosubstitution. For example, the “substituent group where two or moresubstituent groups are connected” may be a biphenyl group. That is, thebiphenyl group may be an aryl group, or may be interpreted as asubstituent group where two phenyl groups are connected.

In the present specification,

means a portion bonded to another substituent group or a bondingportion.

In the present specification, a halogen group may be fluorine, chlorine,bromine or iodine.

In the present specification, the number of carbon atoms of an imidegroup is not particularly limited but is preferably 1 to 30.Specifically, the imide group may be compounds having the followingstructures, but is not limited thereto.

In the present specification, one or two nitrogen atoms of an amidegroup may be substituted by hydrogen, a straight-chained,branched-chained, or cyclic-chained alkyl group having 1 to 30 carbonatoms, or an aryl group having 6 to 30 carbon atoms. Specifically, theamide group may be compounds having the following Structural Formulas,but is not limited thereto.

In the present specification, an alkyl group may be a straight orbranched chain, and the number of carbon atoms thereof is notparticularly limited but is preferably 1 to 30. Specific examplesthereof include methyl, ethyl, propyl, n-propyl, isopropyl, butyl,n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl,pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl,1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl,2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl,cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl,2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl,1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl,4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.

In the present specification, a cycloalkyl group is not particularlylimited, but the number of carbon atoms thereof is preferably 3 to 30,and specific examples thereof include cyclopropyl, cyclobutyl,cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl,3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl,3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl,cyclooctyl, and the like, but are not limited thereto.

In the present specification, the alkoxy group may be a straight,branched, or cyclic chain. The number of carbon atoms of the alkoxygroup is not particularly limited, but preferably 1 to 30. Specificexamples thereof may include methoxy, ethoxy, n-propoxy, isopropoxy,i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy,neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy,2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy,p-methylbenzyloxy, and the like, but are not limited thereto.

In the present specification, the alkenyl group may be a straight orbranched chain, and the number of carbon atoms thereof is notparticularly limited but is preferably 2 to 30. Specific examplesthereof include vinyl, 1-prophenyl, isoprophenyl, 1-butenyl, 2-butenyl,3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl,1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl,2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl,2,2-bis(diphenyl-1-yl)vinyl-1-yl, a stilbenyl group, a styrenyl group,and the like, but are not limited thereto.

In the present specification, an amine group may be selected from thegroup consisting of —NH₂; an alkylamine group; an aralkylamine group; anarylamine group; and a heteroarylamine group, and the number of carbonatoms thereof is not particularly limited, but is preferably 1 to 30.Specific examples of the amine group include a methylamine group, adimethylamine group, an ethylamine group, a diethylamine group, aphenylamine group, a naphthylamine group, a biphenylamine group, ananthracenylamine group, a 9-methyl-anthracenylamine group, adiphenylamine group, a phenylnaphthylamine group, a ditolylamine group,a phenyltolylamine group, a triphenylamine group, and the like, but arenot limited thereto.

In the case where the aryl group is the monocyclic aryl group, thenumber of carbon atoms thereof is not particularly limited but ispreferably 6 to 25. Specific examples of the monocyclic aryl group mayinclude a phenyl group, a biphenyl group, a terphenyl group, and thelike, but are not limited thereto.

In the case where the aryl group is the polycyclic aryl group, thenumber of carbon atoms thereof is not particularly limited but ispreferably 10 to 24. Specific examples of the polycyclic aryl group mayinclude a naphthyl group, a triphenylenyl group, an anthracenyl group, aphenanthryl group, a pyrenyl group, a perylenyl group, a chrysenylgroup, a fluorenyl group, and the like, but are not limited thereto.

In the present specification, the fluorenyl group may be substituted,and the adjacent substituent groups may be bonded to each other to forma cycle.

In the case where the fluorenyl group is substituted,

and the like may be formed. However, the fluorenyl group is not limitedthereto.

In the present specification, the heterocyclic group includes an atomother than carbon, that is, one or more heteroatoms, and specifically,the heteroatom may include one or more atoms selected from the groupconsisting of O, N, Se, S, and the like. The number of carbon atomsthereof is not particularly limited, but preferably 2 to 60. Examples ofthe heterocyclic group include a thiophene group, a furan group, apyrrole group, an imidazole group, a thiazole group, an oxazol group, anoxadiazol group, a triazol group, a pyridyl group, a bipyridyl group, apyrimidyl group, a triazine group, a triazole group, an acridyl group, apyridazine group, a pyrazinyl group, a quinolinyl group, a quinazolinegroup, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinylgroup, a pyridopyrazinyl group, a pyrazinopyrazinyl group, anisoquinoline group, an indole group, a carbazole group, a benzoxazolegroup, a benzimidazole group, a benzothiazol group, a benzocarbazolegroup, a benzothiophene group, a dibenzothiophene group, a benzofuranylgroup, a phenanthroline group, a thiazolyl group, an isoxazolyl group,an oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, aphenothiazinyl group, a dibenzofuranyl group, and the like, but are notlimited thereto.

The heterocyclic group may be a monocycle or a polycycle, and may bearomatics, aliphatics, or a condensation cycle of the aromatics and thealiphatics.

In the present specification, the heteroaryl group may be selected fromthe aforementioned examples of the heterocyclic group.

In the present specification, the arylene group means a matter where twobonding positions exist at the aryl group, that is, a divalent group.Except that the groups are each the divalent group, the aforementioneddescription of the aryl group may be applied thereto.

In the present specification, an aromatic cycle may be a monocyclic or apolycycle, and may be selected from the aforementioned examples of thearyl group, except that the aromatic cycle is not monovalent.

In the present specification, the heterocycle may be an aliphatic cycleor an aromatic cycle, means a matter in which at least one carbon atomof the aliphatic or aromatic cycle is substituted by a N, O, or S atom,may be a monocycle or a polycycle, and may be selected from theaforementioned examples of the heteroaryl group, except that theheterocycle is not monovalent.

In the present specification, the “adjacent” group may mean asubstituent group substituted in an atom directly connected to an atomwhere the corresponding substituent group is substituted, a substituentgroup that is positioned sterically closest to the correspondingsubstituent group, or another substituent group substituted in an atomwhere the corresponding substituent group is substituted. For example,two substituent groups substituted at an ortho position in a benzenecycle and two substituent groups substituted at the same carbon in thealiphatic cycle may be interpreted as the groups “adjacent” to eachother.

In the present specification, formation of the aromatic cycle by bondingthe adjacent groups to each other means formation of a 5-membered to8-membered monocyclic or polycyclic aromatic cycle by forming a bondbetween the adjacent substituent groups, and the aromatic cycle may beselected from the aforementioned examples of the aryl group.Specifically, according to the exemplary embodiment of the presentspecification, the adjacent groups may be bonded to each other to form afluorene structure.

According to the exemplary embodiment of the present specification, inChemical Formula 1, at least one of X1 to X3 is N.

In the exemplary embodiment of the present specification, X1 may be Nand X2 and X3 may be CH.

In the exemplary embodiment of the present specification, X2 may be Nand X1 and X3 may be CH.

In the exemplary embodiment of the present specification, X3 may be Nand X1 and X2 may be CH.

According to another exemplary embodiment of the present specification,at least two of X1 to X3 are N.

In the exemplary embodiment of the present specification, X1 and X2 maybe N. In this case, X3 is CH.

In the exemplary embodiment of the present specification, X1 and X3 maybe N. In this case, X2 is CH.

In the exemplary embodiment of the present specification, X2 and X3 maybe N. In this case, X1 is CH.

According to another exemplary embodiment of the present specification,X1 to X3 are N.

According to the exemplary embodiment of the present specification, inChemical Formula 1, Cy1 and Cy2 are the same as or different from eachother, and are each independently a substituted or unsubstitutedmonocyclic or polycyclic aromatic cycle having 6 to 20 carbon atoms; ora substituted or unsubstituted monocyclic or polycyclic heterocyclehaving 2 to 20 carbon atoms.

According to another exemplary embodiment of the present specification,Cy1 and Cy2 are the same as or different from each other, and are eachindependently a substituted or unsubstituted monocyclic or polycyclicaromatic cycle having 6 to 10 carbon atoms; or a substituted orunsubstituted monocyclic or polycyclic heterocycle having 2 to 10 carbonatoms.

According to another exemplary embodiment of the present specification,Cy1 and Cy2 are the same as or different from each other, and are eachindependently a substituted or unsubstituted benzene cycle; or asubstituted or unsubstituted naphthalene cycle.

According to another exemplary embodiment of the present specification,Cy1 and Cy2 are the same as or different from each other, and are eachindependently a benzene cycle; or a naphthalene cycle.

According to one exemplary embodiment of the present specification, atleast one of Cy1 and Cy2 is a substituted or unsubstituted benzenecycle.

According to the exemplary embodiment of the present specification, thecompound represented by Chemical Formula 1 is represented by any one ofthe following Chemical Formulas 1-1 to 1-4.

In Chemical Formulas 1-1 to 1-4,

X1 to X3, L1, m, Ar1, and Ar2 are the same as those defined in ChemicalFormula 1,

Z1 is deuterium,

p′ is an integer of 0 to 8, and

p is an integer of 0 to 10.

According to the exemplary embodiment of the present specification,Chemical Formula 1 is represented by the following Chemical Formula 1-5.

In Chemical Formula 1-5, Cyt, Cy2, L1, m, Ar1, and Ar2 are the same asdefined in Chemical Formula 1 according to the aforementioned exemplaryembodiment.

According to the exemplary embodiment of the present specification, inChemical Formula 1, L1 is a substituted or unsubstituted monocyclic orpolycyclic arylene group having 6 to 30 carbon atoms.

According to the exemplary embodiment of the present specification, inChemical Formula 1, L1 is a substituted or unsubstituted monocyclicarylene group having 6 to 30 carbon atoms. In this case, L1 may help aninteraction between a structure including Cy1 and Cy2 and a structureincluding X1 to X3 to help the bipolar type to be stably maintained.

According to another exemplary embodiment of the present specification,L1 is a substituted or unsubstituted monocyclic arylene group having 6to 24 carbon atoms.

According to another exemplary embodiment of the present specification,L1 is a substituted or unsubstituted phenylene group; or a substitutedor unsubstituted biphenylene group.

According to another exemplary embodiment of the present specification,L1 is a substituted or unsubstituted phenylene group; a substituted orunsubstituted biphenylene group; a substituted or unsubstitutedterphenylene group; or a substituted or unsubstituted quaterphenylenegroup.

According to one exemplary embodiment of the present specification, m is1.

According to another exemplary embodiment, m is 2.

According to another exemplary embodiment, m is 3.

According to another exemplary embodiment, m is 4.

According to another exemplary embodiment of the present specification,L1 is a phenylene group; a biphenylene group; a terphenylene group; or aquaterphenylene group.

According to another exemplary embodiment of the present specification,L1 is a phenylene group; or a biphenylene group, and m is 1 or 2, and inthe case where m is 2, L1s are the same as or different from each other.

In one exemplary embodiment of the present specification, (L1)_(m) isrepresented by the following Chemical Formula 3.

In Chemical Formula 3,

R is a substituent group,

a is an integer of 1 to 4,

in the case where a is an integer of 2 to 4, 2 to 4 Rs are the same asor different from each other,

m is an integer of 1 to 4, and

in the case where m is an integer of 2 to 4, 2 to 4 structures inbrackets are the same as or different from each other.

The substituent group R may be selected from the aforementioned examplesof the substituent group.

According to the exemplary embodiment of the present specification, inthe case where (L1)_(m) is Chemical Formula 3, a cycle including Cy1 andCy2 and a cycle including X1 to X3 may be connected in a linear form tostructurally connect the p type and the n type and thus increase aninteraction thereof, thereby stably serving as the bipolar type.

According to the exemplary embodiment of the present specification, thecompound represented by Chemical Formula 1 is represented by any one ofthe following Chemical Formulas 1-6 to 1-9.

In Chemical Formulas 1-6 to 1-9,

X1 to X3 are the same as or different from each other, and are eachindependently N or CH,

at least one of X1 to X3 is N,

Ar5 and Ar6 are the same as or different from each other, and are eachindependently hydrogen; deuterium; a substituted or unsubstituted alkylgroup having 1 to 20 carbon atoms; a substituted or unsubstitutedmonocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or asubstituted or unsubstituted monocyclic or polycyclic heteroaryl grouphaving 2 to 30 carbon atoms, or are bonded to a phenyl group to form acycle,

R is a substituent group,

a is an integer of 1 to 4,

in the case where a is an integer of 2 to 4, 2 to 4 Rs are the same asor different from each other,

m is an integer of 1 to 4, and

in the case where m is an integer of 2 to 4, 2 to 4 structures inbrackets are the same as or different from each other.

According to another exemplary embodiment of the present specification,Ar5 and Ar6 are the same as or different from each other, and are eachindependently hydrogen; deuterium; a substituted or unsubstituted alkylgroup having 1 to 10 carbon atoms; a substituted or unsubstitutedmonocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or asubstituted or unsubstituted monocyclic or polycyclic heteroaryl grouphaving 2 to 20 carbon atoms, or are bonded to a phenyl group to form acycle.

According to another exemplary embodiment of the present specification,Ar5 and Ar6 are the same as or different from each other, and are eachindependently hydrogen; deuterium; a substituted or unsubstituted alkylgroup having 1 to 5 carbon atoms; a substituted or unsubstitutedmonocyclic or polycyclic aryl group having 6 to 10 carbon atoms; or asubstituted or unsubstituted monocyclic or polycyclic heteroaryl grouphaving 2 to 10 carbon atoms, or are bonded to a phenyl group to form acycle.

Formation of the cycle by bonding to the phenyl group means formation ofa condensation cycle by bonding the phenyl group and Ar5 or Ar6, and inthis case, the structure including X1 to X3 may be substituted by apolycycle. In the present specification, the cycle may be an aliphatichydrocarbon cycle, an aromatic hydrocarbon cycle, an aliphaticheterocycle, an aromatic heterocycle, or the like.

According to another exemplary embodiment of the present specification,Ar5 and Ar6 are the same as or different from each other, and are eachindependently hydrogen; a substituted or unsubstituted methyl group; asubstituted or unsubstituted phenyl group; a substituted orunsubstituted biphenyl group; or a substituted or unsubstituted naphthylgroup, or are bonded to a phenyl group to form a substituted orunsubstituted naphthalene cycle, a substituted or unsubstitutedtriphenylene cycle, a substituted or unsubstituted fluorene cycle; or asubstituted or unsubstituted phenanthrene cycle.

According to another exemplary embodiment of the present specification,Ar5 and Ar6 are the same as or different from each other, and are eachindependently a methyl group; a triphenylmethyl group; a phenyl group; anaphthyl group; or a biphenyl group, or are bonded to a phenyl group toform a naphthalene cycle; a triphenylene cycle; a fluorene cyclesubstituted by a phenyl group; or a phenanthrene cycle.

According to the exemplary embodiment of the present specification, inChemical Formula 1, Ar1 and Ar2 are the same as or different from eachother, and are each independently selected from the group consisting ofa substituted or unsubstituted monocyclic or polycyclic aryl grouphaving 6 to 20 carbon atoms; and a substituted or unsubstitutedmonocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms.

According to another exemplary embodiment of the present specification,Ar1 and Ar2 are the same as or different from each other, and are eachindependently a substituted or unsubstituted phenyl group; a substitutedor unsubstituted biphenyl group; a substituted or unsubstitutedterphenyl group; a substituted or unsubstituted naphthyl group; asubstituted or unsubstituted triphenylenyl group; a substituted orunsubstituted fluorenyl group; or a substituted or unsubstitutedphenanthrenyl group.

According to another exemplary embodiment of the present specification,Ar1 and Ar2 are the same as or different from each other, and are eachindependently a phenyl group; a biphenyl group; a terphenyl group; anaphthyl group; a triphenylenyl group; a fluorenyl group; or aphenanthrenyl group, and the phenyl group, the biphenyl group, theterphenyl group, the naphthyl group, the triphenylenyl group, thefluorenyl group, and the threnyl group are unsubstituted or substitutedby one or two or more substituent groups selected from the groupconsisting of a substituted or unsubstituted alkyl group and asubstituted or unsubstituted aryl group.

According to another exemplary embodiment of the present specification,Ar1 and Ar2 are the same as or different from each other, and are eachindependently selected from the group consisting of a phenyl group; aphenyl group substituted by a methyl group; a phenyl group substitutedby a triphenylmethyl group; a phenyl group substituted by a naphthylgroup; a phenyl group substituted by a phenyl group; a phenyl groupsubstituted by a terphenyl group; a biphenyl group; a biphenyl groupsubstituted by a phenyl group; a naphthyl group; a triphenylenyl group;a fluorenyl group substituted by a phenyl group; and a phenanthrenylgroup.

According to the exemplary embodiment of the present specification, Ar1and Ar2 are the same as or different from each other, and are eachindependently any one of the following substituent groups.

is a portion connected to the cycle including X1 to X3 of ChemicalFormula 1.

According to the exemplary embodiment of the present specification, p′is 0.

According to one exemplary embodiment, p is 0.

According to the exemplary embodiment of the present specification, thecompound represented by Chemical Formula 1 is represented by any one ofthe following compounds.

According to one exemplary embodiment, the compound represented byChemical Formula 1-1 is represented by any one of the following ChemicalFormulas 1-1-1 to 1-1-37.

According to another exemplary embodiment, the compound represented byChemical Formula 1-2 is represented by any one of the following ChemicalFormulas 1-2-1 to 1-2-8.

According to another exemplary embodiment, the compound represented byChemical Formula 1-3 is represented by any one of the following ChemicalFormulas 1-3-1 to 1-3-8.

According to another exemplary embodiment, the compound represented byChemical Formula 1-4 is represented by any one of the following ChemicalFormulas 1-4-1 to 1-4-8.

According to the exemplary embodiment of the present specification, inChemical Formula 2, Ar3 and Ar4 are the same as or different from eachother, and are a substituted or unsubstituted monocyclic or polycyclicaryl group having 6 to 20 carbon atoms; or a substituted orunsubstituted monocyclic or polycyclic heteroaryl group having 2 to 20carbon atoms.

According to another exemplary embodiment of the present specification,Ar3 and Ar4 are the same as or different from each other, and are asubstituted or unsubstituted monocyclic or polycyclic aryl group having6 to 15 carbon atoms; or a substituted or unsubstituted monocyclic orpolycyclic heteroaryl group having 2 to 15 carbon atoms.

According to another exemplary embodiment of the present specification,Ar3 and Ar4 are the same as or different from each other, and are asubstituted or unsubstituted phenyl group; a substituted orunsubstituted biphenyl group; or a substituted or unsubstitutedfluorenyl group.

According to another exemplary embodiment of the present specification,Ar3 and Ar4 are the same as or different from each other, and are aphenyl group; a phenyl group substituted by a phenyl group; a phenylgroup substituted by a pyridine group; a biphenyl group; or a fluorenylgroup substituted by a methyl group.

According to the exemplary embodiment of the present specification, Ar3is a substituted or unsubstituted phenyl group; a substituted orunsubstituted biphenyl group; or a substituted or unsubstitutedfluorenyl group.

In one exemplary embodiment of the present specification, Ar3 is asubstituted or unsubstituted phenyl group.

In another exemplary embodiment, Ar3 is a phenyl group substituted by anaryl group.

In the exemplary embodiment of the present specification, Ar3 is aphenyl group substituted by a phenyl group.

In another exemplary embodiment, Ar3 is a phenyl group.

In the exemplary embodiment of the present specification, Ar3 is aphenyl group substituted by a heterocyclic group.

In another exemplary embodiment, Ar3 is a phenyl group substituted by anitrogen-containing heterocyclic group.

In another exemplary embodiment, Ar3 is a phenyl group substituted by apyridine group.

In the exemplary embodiment of the present specification, a phenyl groupsubstituted by the pyridine group is

In another exemplary embodiment, Ar3 is a substituted or unsubstitutedbiphenyl group.

In another exemplary embodiment, Ar3 is a phenyl group.

In the exemplary embodiment of the present specification, the biphenylgroup is

In the exemplary embodiment of the present specification, Ar3 is asubstituted or unsubstituted fluorenyl group.

In another exemplary embodiment, Ar3 is a fluorenyl group substituted byan alkyl group.

In the exemplary embodiment of the present specification, Ar3 is afluorenyl group substituted by a methyl group.

According to one exemplary embodiment of the present specification, Ar4is a substituted or unsubstituted phenyl group; or a substituted orunsubstituted biphenyl group.

In one exemplary embodiment, Ar4 is a substituted or unsubstitutedphenyl group.

In another exemplary embodiment, Ar4 is a phenyl group.

In another exemplary embodiment, Ar4 is a substituted or unsubstitutedbiphenyl group.

In another exemplary embodiment, Ar4 is a biphenyl group.

According to the exemplary embodiment of the present specification, inChemical Formula 2, L2 is a substituted or unsubstituted monocyclic orpolycyclic arylene group having 6 to 20 carbon atoms.

According to another exemplary embodiment of the present specification,L2 is a substituted or unsubstituted monocyclic or polycyclic arylenegroup having 6 to 10 carbon atoms.

According to another exemplary embodiment of the present specification,L2 is a substituted or unsubstituted phenylene group; a substituted orunsubstituted biphenylene group; or a substituted or unsubstitutednaphthalene group, or n is 0.

According to the exemplary embodiment of the present specification,(L2)_(n) is a direct bond; a substituted or unsubstituted phenylenegroup; a substituted or unsubstituted biphenylene group; or asubstituted or unsubstituted naphthalene group.

According to the exemplary embodiment of the present specification,(L2)_(n) is a direct bond; a phenylene group; a biphenylene group; or anaphthalene group.

According to the exemplary embodiment of the present specification, inChemical Formula 2, R1 to R7 are the same as or different from eachother, and are each independently selected from the group consisting ofhydrogen; deuterium; a substituted or unsubstituted straight-chained orbranch-chained alkyl group having 1 to 20 carbon atoms; a substituted orunsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbonatoms; and a substituted or unsubstituted monocyclic or polycyclicheteroaryl group having 2 to 20 carbon atoms.

According to another exemplary embodiment of the present specification,R1 to R7 are the same as or different from each other, and are eachindependently selected from the group consisting of hydrogen; deuterium;a substituted or unsubstituted straight-chained or branch-chained alkylgroup having 1 to 10 carbon atoms; a substituted or unsubstitutedmonocyclic or polycyclic aryl group having 6 to 10 carbon atoms; and asubstituted or unsubstituted monocyclic or polycyclic heteroaryl grouphaving 2 to 10 carbon atoms.

According to one exemplary embodiment of the present specification, R1to R7 are the same as or different from each other, and are eachindependently hydrogen; or a substituted or unsubstituted monocyclic orpolycyclic aryl group having 6 to 30 carbon atoms.

According to another exemplary embodiment, R1 to R7 are the same as ordifferent from each other, and are each independently hydrogen; or asubstituted or unsubstituted phenyl group.

In the exemplary embodiment of the present specification, R1 ishydrogen.

In another exemplary embodiment, R2 is hydrogen.

In the exemplary embodiment of the present specification, R3 ishydrogen.

In the exemplary embodiment of the present specification, R4 ishydrogen.

In the exemplary embodiment of the present specification, R5 ishydrogen.

In another exemplary embodiment, R5 is a substituted or unsubstitutedmonocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

In another exemplary embodiment, R5 is a substituted or unsubstitutedphenyl group.

In another exemplary embodiment, R5 is a phenyl group.

In the exemplary embodiment of the present specification, R6 ishydrogen.

In another exemplary embodiment, R7 is hydrogen.

According to the exemplary embodiment of the present specification, inChemical Formula 2, Y1 and Y2 are the same as or different from eachother, and are each independently a substituted or unsubstitutedstraight-chained or branch-chained alkyl group having 1 to 20 carbonatoms; a substituted or unsubstituted monocyclic or polycyclic arylgroup having 6 to 20 carbon atoms; or a substituted or unsubstitutedmonocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms,or Y1 and Y2 are bonded to each other to form a substituted orunsubstituted aromatic cycle.

According to another exemplary embodiment of the present specification,Y1 and Y2 are the same as or different from each other, and are eachindependently a substituted or unsubstituted straight-chained orbranch-chained alkyl group having 1 to 15 carbon atoms; a substituted orunsubstituted monocyclic or polycyclic aryl group having 6 to 15 carbonatoms; or a substituted or unsubstituted monocyclic or polycyclicheteroaryl group having 2 to 15 carbon atoms, or Y1 and Y2 are bonded toeach other to form a substituted or unsubstituted aromatic cycle.

According to another exemplary embodiment of the present specification,Y1 and Y2 are the same as or different from each other, and are eachindependently a substituted or unsubstituted alkyl group having 1 to 10carbon atoms; or a substituted or unsubstituted phenyl group, or arebonded to each other to form a substituted or unsubstituted fluorenestructure.

According to another exemplary embodiment of the present specification,Y1 and Y2 are the same as or different from each other, and are eachindependently a methyl group; or a phenyl group, or are bonded to eachother to form a fluorene structure.

According to one exemplary embodiment of the present specification, inthe case where Y1 and Y2 are bonded to each other to form the fluorenestructure, the fluorenyl group including Y1 and Y2 of Chemical Formula 2may have a spirobifluorene structure.

According to the exemplary embodiment of the present specification, thecompound represented by Chemical Formula 2 is represented by any one ofthe following Chemical Formulas 2-1 to 2-22.

In the exemplary embodiment of the present specification, the organicmaterial layer including the compound represented by Chemical Formula 1is the electron transport layer, the compound represented by ChemicalFormula 1 is represented by Chemical Formula 1-1-19, the organicmaterial layer including the compound represented by Chemical Formula 2is the hole transport layer, and the compound represented by ChemicalFormula 2 is represented by Chemical Formula 2-3.

The organic light emitting diode of the present specification may bemanufactured by a material and a method known in the art, except thatthe electron transport layer and the hole transport layer are included.

For example, the organic light emitting diode of the presentspecification may be manufactured by sequentially laminating the anode,the organic material layer, and the cathode on the substrate. In thiscase, the organic light emitting diode may be manufactured by depositinga metal, metal oxides having conductivity, or an alloy thereof on thesubstrate by using a physical vapor deposition (PVD) method such as asputtering method or an e-beam evaporation method to form the anode,forming the organic material layer including the hole injection layer,the hole transport layer, the electron blocking layer, the lightemitting layer, the electron transport layer, and the electron injectionlayer thereon, and then depositing a material that can be used as thecathode thereon. In addition to the aforementioned method, the organiclight emitting diode may be manufactured by sequentially depositing acathode material, the organic material layer, and an anode material onthe substrate. In addition to the aforementioned method, the organiclight emitting diode may be manufactured by sequentially depositing theanode material, the organic material layer, and the cathode material onthe substrate.

The organic material layer of the organic light emitting diode of thepresent specification may have a multilayered structure where one ormore organic material layers are laminated.

In the exemplary embodiment of the present specification, the organiclight emitting diode may further include one layer or two or more layersselected from the group consisting of the hole injection layer, the holetransport layer, the electron transport layer, the electron injectionlayer, the electron blocking layer, and the hole blocking layer.

For example, the structure of the organic light emitting diode of thepresent specification may have a structure shown in FIGS. 1 and 2, butis not limited thereto.

FIG. 1 illustrates a structure of an organic light emitting diode wherean anode 201, a hole transport layer 301, an electron blocking layer401, a light emitting layer 501, an electron transport layer 601, and acathode 701 are sequentially laminated on a substrate 101. In FIG. 1,the compound represented by Chemical Formula 2 is included in the holetransport layer 301, and the compound represented by Chemical Formula 1is included in the electron transport layer 601.

FIG. 2 illustrates a structure of an organic light emitting diode wherethe anode 201, the hole transport layer 301, the electron blocking layer401, the light emitting layer 501, the electron transport layer 601, anelectron injection layer 801, and the cathode 701 are sequentiallylaminated on the substrate 101. In FIG. 2, the compound represented byChemical Formula 2 may be included in the hole transport layer 301, andthe compound represented by Chemical Formula 1 may be included in theelectron transport layer 601. Further, the compound represented byChemical Formula 2 may be included in the hole transport layer 301, andthe compound represented by Chemical Formula 1 may be included in theelectron injection layer 801. Further, the compound represented byChemical Formula 2 may be included in the hole transport layer 301, andthe compound represented by Chemical Formula 1 may be included in theelectron transport layer 601 and the electron injection layer 801.

FIGS. 1 and 2 are the exemplified structures according to the exemplaryembodiment of the present specification, and may further include otherorganic material layers.

In the case where the organic light emitting diode includes a pluralityof organic material layers, the organic material layers may be formed ofthe same material or different materials.

As the anode material, in general, it is preferable to use a materialhaving a large work function so as to smoothly inject holes into theorganic material layer. Specific examples of the anode material that maybe used in the present invention include metals such as vanadium,chrome, copper, zinc, and gold, or an alloy thereof; metal oxides suchas zinc oxides, indium oxides, indium tin oxides (ITO), and indium zincoxides (IZO); a combination of metals and oxides, such as ZnO:Al orSNO₂:Sb; conductive polymers such as poly(3-methylthiophene),poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, andpolyaniline, and the like, but are not limited thereto.

It is preferable that the cathode material be, in general, a materialhaving a small work function so as to easily inject electrons into theorganic material layer. Specific examples of the cathode materialinclude metals such as magnesium, calcium, sodium, potassium, titanium,indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead,or an alloy thereof; a multilayered structure material such as LiF/Al orLiO₂/Al, and the like, but are not limited thereto.

The hole injection material is a layer injecting the holes from theelectrode, and it is preferable that the hole injection material be acompound which has an ability of transporting the holes to have a holeinjection effect from the anode and an excellent hole injection effectto the light emitting layer or the light emitting material, preventsmovement of an exciton generated in the light emitting layer to theelectron injection layer or the electron injection material, and has anexcellent thin film forming ability. It is preferable that a highestoccupied molecular orbital (HOMO) of the hole injection material bebetween the work function of the anode material and a highest occupiedmolecular orbital (HOMO) of a peripheral organic material layer.Specific examples of the hole injection material include metalporphyrine, oligothiophene, an arylamine-based organic material, ahexanitrilehexaazatriphenylene-based organic material, aquinacridone-based organic material, a perylene-based organic material,anthraquinone, polyaniline, a polythiophene-based conductive polymer,and the like, but are not limited thereto.

The electron blocking layer is a layer which may prevent the holesinjected from the hole injection layer from moving into the electroninjection layer via the light emitting layer to improve a life-span andefficiency of the diode, and if necessary, may be formed in anappropriate portion between the light emitting layer and the electroninjection layer by using a publicly known material.

The light emitting material is a material that receives and combines theholes and the electrons from the hole transport layer and the electrontransport layer, such that light in a visible light region is emitted,and it is preferable to use a material having excellent quantumefficiency to fluorescence or phosphorescence. Specific examples thereofinclude a 8-hydroxy-quinoline aluminum complex (Alq₃); a carbazole-basedcompound; a dimerized styryl compound; BAlq; a10-hydroxybenzoquinoline-metal compound; benzoxazole, benzthiazole, andbenzimidazole-based compounds; a poly(p-phenylenevinylene) (PPV)-basedpolymer; a spiro compound; polyfluorene, lubrene, and the like, but arenot limited thereto.

The light emitting layer may include a host material and a dopantmaterial. Examples of the host material include a condensation aromaticring derivative, a hetero-ring-containing compound, or the like.Specific examples of the compensation aromatic ring derivative includean anthracene derivative, a pyrene derivative, a naphthalene derivative,a pentacene derivative, a phenanthrene compound, a fluoranthenecompound, and the like, and specific examples of thehetero-ring-containing compound include a carbazole derivative, adibenzofuran derivative, a ladder-type furan compound, a pyrimidinederivative, and the like, but the examples are not limited thereto.

Examples of the dopant material include an organic compound, a metal, ora metal compound.

Examples of the organic compound as the dopant material include anaromatic amine derivative, a styrylamine compound, a boron complex, afluoranthene compound, and the like. Specifically, the aromatic aminederivative is a compensation aromatic ring derivative having asubstituted or unsubstituted arylamino group, examples thereof includepyrene, anthracene, chrysene, and periflanthene having the arylaminogroup, the styrylamine compound is a compound where at least onearylvinyl group is substituted in substituted or unsubstitutedarylamine, and in the styrylamine compound, one or two or moresubstituent groups selected from the group consisting of an aryl group,a silyl group, an alkyl group, a cycloalkyl group, and an arylaminogroup are substituted or unsubstituted. Specific examples thereofinclude styrylamine, styryldiamine, styryltriamine, styryltetraamine,and the like, but are not limited thereto. Further, a general metal ormetal compound may be used as the metal or the metal compound, andspecifically, a metal complex may be used. Further, examples of themetal complex include an iridium complex, a platinum complex, and thelike, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinatolithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper,bis(8-hydroxyquinolinato)manganese, tris(8-hydroxyquinolinato)aluminum,tris(2-methyl-8-hydroxyquinolinato)aluminum,tris(8-hydroxyquinolinato)gallium,bis(10-hydroxybenzo[h]quinolinato)beryllium,bis(10-hydroxybenzo[h]quinolinato)zinc,bis(2-methyl-8-quinolinato)chlorogallium,bis(2-methyl-8-quinolinato)(o-cresolato)gallium,bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum,bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, and the like, but arenot limited thereto.

The electron injection layer is a layer injecting the electrons from theelectrode, and a compound which has an ability of transporting theelectrons, an electron injection effect from the cathode, and anexcellent electron injection effect to the light emitting layer or thelight emitting material, prevents movement of an exciton generated inthe light emitting layer to the hole injection layer, and has anexcellent thin film forming ability is preferable. Specific examplesthereof include fluorenone, anthraquinodimethane, diphenoquinone,thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidene methane, anthrone, and the like,and derivatives thereof, a metal complex compound, a nitrogen-containing5-membered cycle derivative, and the like, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinatolithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper,bis(8-hydroxyquinolinato)manganese, tris(8-hydroxyquinolinato)aluminum,tris(2-methyl-8-hydroxyquinolinato)aluminum,tris(8-hydroxyquinolinato)gallium,bis(10-hydroxybenzo[h]quinolinato)beryllium,bis(10-hydroxybenzo[h]quinolinato)zinc,bis(2-methyl-8-quinolinato)chlorogallium,bis(2-methyl-8-quinolinato)(o-cresolato)gallium,bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum,bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, and the like, but arenot limited thereto.

The hole blocking layer is a layer preventing holes from reaching thecathode, and in general, may be formed under the same condition as thehole injection layer. Specific examples thereof include an oxadiazolederivative, a triazole derivative, a phenanthroline derivative,2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), an aluminumcomplex, and the like, but are not limited thereto.

The organic light emitting diode according to the present specificationmay be a top emission type, a bottom emission type, or a both-sidedemission type according to the used material.

Further, the organic light emitting diode according to the presentspecification may be a normal type where a lower electrode is the anodeand an upper electrode is the cathode, or may be an inverted type wherethe lower electrode is the cathode and the upper electrode is the anode.

The structure according to the exemplary embodiment of the presentspecification may act even in an organic electronic diode including anorganic solar cell, an organic photoconductor, an organic transistor,and the like by the principle that is similar to the principle appliedto the organic light emitting diode.

Hereinafter, the present specification will be described in detailthrough Examples. However, the Examples according to the presentspecification may be modified in various other forms, and the scope ofthe present specification is not interpreted to be limited to theExamples described in detail below. The Examples of the presentspecification are provided so that a person with ordinary skill in theart may fully understand the present specification.

EXAMPLE Example 1 Manufacturing of Organic Light Emitting Diode

The glass substrate (corning 7059 glass) on which the thin film of ITO(indium tin oxide) was applied at a thickness of 1,000 Å was immersed indistilled water having the detergent dissolved therein, and washed bythe ultrasonic wave. In this case, the detergent used herein was theproduct commercially available from Fischer Co. and distilled water usedherein was one which had been twice filtered by using the filtercommercially available from Millipore Co. ITO was washed for 30 minutes,and washing with ultrasonic waves was then repeated twice for 10 minutesby using distilled water. After the completion of washing with distilledwater, washing with ultrasonic waves was performed by using solventssuch as isopropyl alcohol, acetone, and methanol, and the resultingproduct was dried and transported to the plasma washing machine.Further, the substrate was dry-washed by using the oxygen plasma for 5minutes, and then transported to the vacuum deposition machine.

Hexanitrile hexaazatriphenylene (hereinafter, referred to as “HAT”) thatwas the compound of the following Chemical Formula was deposited underthe heat vacuum in a thickness of 500 Å on the prepared ITO transparentelectrode to form the thin film. The interfacial property between thesubstrate and the hole injection layer can be improved by this thinfilm. Subsequently, the compound of Chemical Formula 2-3 was depositedin a thickness of 400 Å on the thin film to form the hole transportlayer, and the compound of the following EB-1 was deposited in athickness of 250 Å thereon to form the electron blocking layer. Thecompound of the following H1 as the host of the light emitting layer andthe compound of the following D1 as the dopant were deposited under thevacuum in a thickness of 200 Å thereon. The electron transport layermaterial of Chemical Formula 1-1-1 and lithium quinolate (LiQ) weredeposited under vacuum as at a weight ratio of 1:1 on the light emittinglayer to form the electronic injection and transport layer in athickness of 300 Å. Lithium fluoride (LiF) in a thickness of 12 Å andaluminum in a thickness of 2,000 Å were subsequently deposited on theelectron transport layer to form the cathode.

In the aforementioned process, the deposition rate of the organicmaterial was maintained at 0.3 to 0.8 Å/sec. Further, the depositionrate of lithium fluoride of the cathode was maintained at 0.3 Å/sec, andthe deposition rate of aluminum was maintained at 1.5 to 2.5 Å/sec. Thedegree of vacuum during deposition was maintained at 1 to 3×10⁻⁷.

Example 2 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 1, except that Chemical Formula 2-6 was used instead of ChemicalFormula 2-3 in Example 1.

Example 3 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 1, except that Chemical Formula 2-13 was used instead ofChemical Formula 2-3 in Example 1.

Example 4 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 1, except that Chemical Formula 2-17 was used instead ofChemical Formula 2-3 in Example 1.

Example 5 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 1, except that Chemical Formula 1-1-2 was used instead ofChemical Formula 1-1-1 in Example 1.

Example 6 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 2, except that Chemical Formula 1-1-2 was used instead ofChemical Formula 1-1-1 in Example 2.

Example 7 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 3, except that Chemical Formula 1-1-2 was used instead ofChemical Formula 1-1-1 in Example 3.

Example 8 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 4, except that Chemical Formula 1-1-2 was used instead ofChemical Formula 1-1-1 in Example 4.

Example 9 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 1, except that Chemical Formula 1-1-27 was used instead ofChemical Formula 1-1-1 in Example 1.

Example 10 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 2, except that Chemical Formula 1-1-27 was used instead ofChemical Formula 1-1-1 in Example 2.

Example 11 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 3, except that Chemical Formula 1-1-27 was used instead ofChemical Formula 1-1-1 in Example 3.

Example 12 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 4, except that Chemical Formula 1-1-27 was used instead ofChemical Formula 1-1-1 in Example 4.

Example 13 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 1, except that Chemical Formula 1-1-17 was used instead ofChemical Formula 1-1-1 in Example 1.

Example 14 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 2, except that Chemical Formula 1-1-17 was used instead ofChemical Formula 1-1-1 in Example 2.

Example 15 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 3, except that Chemical Formula 1-1-17 was used instead ofChemical Formula 1-1-1 in Example 3.

Example 16 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 4, except that Chemical Formula 1-1-17 was used instead ofChemical Formula 1-1-1 in Example 4.

Example 17 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 1, except that Chemical Formula 1-1-19 was used instead ofChemical Formula 1-1-1 in Example 1.

Example 18 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 2, except that Chemical Formula 1-1-19 was used instead ofChemical Formula 1-1-1 in Example 2.

Example 19 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 3, except that Chemical Formula 1-1-19 was used instead ofChemical Formula 1-1-1 in Example 3.

Example 20 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 4, except that Chemical Formula 1-1-19 was used instead ofChemical Formula 1-1-1 in Example 4.

Example 21 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 1, except that Chemical Formula 1-4-4 was used instead ofChemical Formula 1-1-1 in Example 1.

Example 22 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 2, except that Chemical Formula 1-4-4 was used instead ofChemical Formula 1-1-1 in Example 2.

Example 23 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 3, except that Chemical Formula 1-4-4 was used instead ofChemical Formula 1-1-1 in Example 3.

Example 24 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 4, except that Chemical Formula 1-4-4 was used instead ofChemical Formula 1-1-1 in Example 4.

Comparative Example 1 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 1, except that the following Chemical Formula ET-1 was usedinstead of Chemical Formula 1-1-1 in Example 1.

Comparative Example 2 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 2, except that Chemical Formula ET-1 was used instead ofChemical Formula 1-1-1 in Example 2.

Comparative Example 3 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 3, except that Chemical Formula ET-1 was used instead ofChemical Formula 1-1-1 in Example 3.

Comparative Example 4 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 4, except that Chemical Formula ET-1 was used instead ofChemical Formula 1-1-1 in Example 4.

Comparative Example 5 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 1, except that the following Chemical Formula ET-2 was usedinstead of Chemical Formula 1-1-1 in Example 1.

Comparative Example 6 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 2, except that Chemical Formula ET-2 was used instead ofChemical Formula 1-1-1 in Example 2.

Comparative Example 7 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 3, except that Chemical Formula ET-2 was used instead ofChemical Formula 1-1-1 in Example 3.

Comparative Example 8 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 4, except that Chemical Formula ET-2 was used instead ofChemical Formula 1-1-1 in Example 4.

Comparative Example 9 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 1, except that the following Chemical Formula ET-3 was usedinstead of Chemical Formula 1-1-1 in Example 1.

Comparative Example 10 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 2, except that Chemical Formula ET-3 was used instead ofChemical Formula 1-1-1 in Example 2.

Comparative Example 11 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 3, except that Chemical Formula ET-3 was used instead ofChemical Formula 1-1-1 in Example 3.

Comparative Example 12 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 4, except that Chemical Formula ET-3 was used instead ofChemical Formula 1-1-1 in Example 4.

Comparative Example 13 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 1, except that the following Chemical Formula ET-4 was usedinstead of Chemical Formula 1-1-1 in Example 1.

Comparative Example 14 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 2, except that Chemical Formula ET-4 was used instead ofChemical Formula 1-1-1 in Example 2.

Comparative Example 15 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 3, except that Chemical Formula ET-4 was used instead ofChemical Formula 1-1-1 in Example 3.

Comparative Example 16 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 4, except that Chemical Formula ET-4 was used instead ofChemical Formula 1-1-1 in Example 4.

Comparative Example 17 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 1, except that the following Chemical Formula ET-5 was usedinstead of Chemical Formula 1-1-1 in Example 1.

Comparative Example 18 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 2, except that Chemical Formula ET-5 was used instead ofChemical Formula 1-1-1 in Example 2.

Comparative Example 19 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 3, except that Chemical Formula ET-5 was used instead ofChemical Formula 1-1-1 in Example 3.

Comparative Example 20 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 4, except that Chemical Formula ET-5 was used instead ofChemical Formula 1-1-1 in Example 4.

Comparative Example 21 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 1, except that the following Chemical Formula ET-6 was usedinstead of Chemical Formula 1-1-1 in Example 1.

Comparative Example 22 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 2, except that Chemical Formula ET-6 was used instead ofChemical Formula 1-1-1 in Example 2.

Comparative Example 23 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 3, except that Chemical Formula ET-6 was used instead ofChemical Formula 1-1-1 in Example 3.

Comparative Example 24 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 4, except that Chemical Formula ET-6 was used instead ofChemical Formula 1-1-1 in Example 4.

Comparative Example 25 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 1, except that the following Chemical Formula HT-1 was usedinstead of Chemical Formula 2-3 in Example 1.

Comparative Example 26 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 5, except that the following Chemical Formula HT-1 was usedinstead of Chemical Formula 2-3 in Example 5.

Comparative Example 27 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 9, except that Chemical Formula HT-1 was used instead ofChemical Formula 2-3 in Example 9.

Comparative Example 28 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 13, except that Chemical Formula HT-1 was used instead ofChemical Formula 2-3 in Example 13.

Comparative Example 29 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 17, except that Chemical Formula HT-1 was used instead ofChemical Formula 2-3 in Example 17.

Comparative Example 30 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 21, except that Chemical Formula HT-1 was used instead ofChemical Formula 2-3 in Example 21.

Comparative Example 31 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 1, except that the following Chemical Formula HT-2 was usedinstead of Chemical Formula 2-3 in Example 1.

Comparative Example 32 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 5, except that the following Chemical Formula HT-2 was usedinstead of Chemical Formula 2-3 in Example 5.

Comparative Example 33 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 9, except that the following Chemical Formula HT-2 was usedinstead of Chemical Formula 2-3 in Example 9.

Comparative Example 34 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 13, except that the following Chemical Formula HT-2 was usedinstead of Chemical Formula 2-3 in Example 13.

Comparative Example 35 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 17, except that the following Chemical Formula HT-2 was usedinstead of Chemical Formula 2-3 in Example 17.

Comparative Example 36 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 21, except that the following Chemical Formula HT-2 was usedinstead of Chemical Formula 2-3 in Example 21.

Comparative Example 37 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 1, except that the compound of ET-1 and Chemical Formula HT-1were used instead of Chemical Formula 1-1-1 and Chemical Formula 2-3 inExample 1.

Comparative Example 38 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 1, except that the compound of ET-1 and Chemical Formula HT-2were used instead of Chemical Formula 1-1-1 and Chemical Formula 2-3 inExample 1.

Comparative Example 39 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 1, except that the compound of ET-2 and Chemical Formula HT-1were used instead of Chemical Formula 1-1-1 and Chemical Formula 2-3 inExample 1.

Comparative Example 40 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 1, except that the compound of ET-2 and Chemical Formula HT-2were used instead of Chemical Formula 1-1-1 and Chemical Formula 2-3 inExample 1.

Comparative Example 41 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 1, except that the compound of ET-3 and Chemical Formula HT-1were used instead of Chemical Formula 1-1-1 and Chemical Formula 2-3 inExample 1.

Comparative Example 42 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 1, except that the compound of ET-3 was used instead of ChemicalFormula 1-1-1 and Chemical Formula HT-2 was used instead of ChemicalFormula 2-3 in Example 1.

Comparative Example 43 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 1, except that the compound of ET-4 and Chemical Formula HT-1were used instead of Chemical Formula 1-1-1 and Chemical Formula 2-3 inExample 1.

Comparative Example 44 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 1, except that the compound of ET-4 and Chemical Formula HT-2were used instead of Chemical Formula 1-1-1 and Chemical Formula 2-3 inExample 1.

Comparative Example 45 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 1, except that the compound of ET-5 and Chemical Formula HT-1were used instead of Chemical Formula 1-1-1 and Chemical Formula 2-3 inExample 1.

Comparative Example 46 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 1, except that the compound of ET-5 and Chemical Formula HT-2were used instead of Chemical Formula 1-1-1 and Chemical Formula 2-3 inExample 1.

Comparative Example 47 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 1, except that the compound of ET-6 and Chemical Formula HT-1were used instead of Chemical Formula 1-1-1 and Chemical Formula 2-3 inExample 1.

Comparative Example 48 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 1, except that the compound of ET-6 and Chemical Formula HT-2were used instead of Chemical Formula 1-1-1 and Chemical Formula 2-3 inExample 1.

Comparative Example 49 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 1, except that the following Chemical Formula ET-7 was usedinstead of Chemical Formula 1-1-1 in Example 1.

Comparative Example 50 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 2, except that Chemical Formula ET-7 was used instead ofChemical Formula 1-1-1 in Example 2.

Comparative Example 51 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 3, except that Chemical Formula ET-7 was used instead ofChemical Formula 1-1-1 in Example 3.

Comparative Example 52 Manufacturing of Organic Light Emitting Diode

The organic light emitting diode was manufactured by the same method asExample 4, except that Chemical Formula ET-7 was used instead ofChemical Formula 1-1-1 in Example 4.

The driving voltage and light emitting efficiency of the organic lightemitting diode manufactured by the aforementioned method were measuredat the current density of 10 mA/cm², and the time (LT98) at whichbrightness was 98% of initial brightness was measured at the currentdensity of 20 mA/cm². The result is described in the following Table 1.

TABLE 1 Current Voltage efficiency Color coordinates Life Time 98 (V)(cd/A) (x, y) at 20 mA/cm² Experimental 4.01 5.54 (0.138, 0.142) 44Example 1 Experimental 4.18 5.76 (0.138, 0.142) 40 Example 2Experimental 4.05 5.56 (0.138, 0.142) 39 Example 3 Experimental 3.945.78 (0.139, 0.143) 35 Example 4 Experimental 3.99 5.52 (0.138, 0.142)43 Example 5 Experimental 4.10 5.68 (0.139, 0.142) 41 Example 6Experimental 4.01 5.58 (0.138, 0.142) 38 Example 7 Experimental 3.885.65 (0.138, 0.143) 34 Example 8 Experimental 4.11 5.64 (0.138, 0.142)42 Example 9 Experimental 4.21 5.87 (0.138, 0.143) 41 Example 10Experimental 4.07 5.66 (0.138, 0.142) 35 Example 11 Experimental 3.995.85 (0.139, 0.142) 31 Example 12 Experimental 4.10 5.55 (0.138, 0.142)47 Example 13 Experimental 4.13 5.35 (0.138, 0.142) 48 Example 14Experimental 4.04 5.79 (0.138, 0.142) 42 Example 15 Experimental 3.985.53 (0.138, 0.142) 33 Example 16 Experimental 4.02 5.44 (0.138, 0.142)41 Example 17 Experimental 4.09 5.51 (0.138, 0.142) 42 Example 18Experimental 4.07 5.35 (0.138, 0.142) 44 Example 19 Experimental 4.035.42 (0.139, 0.143) 45 Example 20 Experimental 4.01 5.77 (0.138, 0.142)45 Example 21 Experimental 4.05 5.76 (0.138, 0.142) 48 Example 22Experimental 4.02 5.76 (0.138, 0.142) 50 Example 23 Experimental 3.855.78 (0.138, 0.142) 49 Example 24 Comparative 4.05 5.14 (0.138, 0.142)25 Example 1 Comparative 4.21 5.05 (0.138, 0.142) 21 Example 2Comparative 4.11 5.01 (0.138, 0.142) 19 Example 3 Comparative 4.03 4.99(0.138, 0.143) 22 Example 4 Comparative 4.03 5.11 (0.138, 0.141) 27Example 5 Comparative 4.18 5.25 (0.137, 0.142) 30 Example 6 Comparative4.09 5.16 (0.138, 0.142) 28 Example 7 Comparative 4.09 5.05 (0.139,0.142) 26 Example 8 Comparative 4.04 4.84 (0.138, 0.142) 26 Example 9Comparative 4.19 5.06 (0.138, 0.142) 22 Example 10 Comparative 4.11 5.03(0.138, 0.141) 20 Example 11 Comparative 4.04 4.89 (0.138, 0.142) 20Example 12 Comparative 4.20 5.31 (0.138, 0.141) 11 Example 13Comparative 4.48 5.24 (0.137, 0.142) 8 Example 14 Comparative 4.39 5.06(0.138, 0.142) 5 Example 15 Comparative 4.59 5.25 (0.139, 0.143) 9Example 16 Comparative 4.00 5.05 (0.138, 0.142) 18 Example 17Comparative 4.05 5.21 (0.139, 0.142) 19 Example 18 Comparative 4.04 5.25(0.138, 0.142) 7 Example 19 Comparative 4.03 5.22 (0.138, 0.142) 15Example 20 Comparative 4.42 4.14 (0.138, 0.152) 12 Example 21Comparative 4.50 3.05 (0.138, 0.146) 15 Example 22 Comparative 5.11 4.05(0.138, 0.144) 16 Example 23 Comparative 5.01 3.98 (0.138, 0.142) 11Example 24 Comparative 4.51 5.02 (0.138, 0.142) 35 Example 25Comparative 4.64 5.24 (0.138, 0.142) 23 Example 26 Comparative 4.60 5.05(0.138, 0.142) 28 Example 27 Comparative 4.75 5.03 (0.138, 0.141) 14Example 28 Comparative 4.55 5.01 (0.138, 0.142) 20 Example 29Comparative 4.62 4.74 (0.138, 0.142) 21 Example 30 Comparative 4.44 5.10(0.138, 0.142) 20 Example 31 Comparative 4.35 5.22 (0.138, 0.142) 19Example 32 Comparative 4.50 5.15 (0.138, 0.142) 18 Example 33Comparative 4.63 5.11 (0.138, 0.141) 15 Example 34 Comparative 4.45 5.01(0.138, 0.142) 21 Example 35 Comparative 4.53 4.99 (0.138, 0.142) 16Example 36 Comparative 4.45 5.02 (0.138, 0.142) 21 Example 37Comparative 4.33 5.09 (0.138, 0.141) 19 Example 38 Comparative 4.34 4.80(0.138, 0.142) 23 Example 39 Comparative 4.90 5.01 (0.138, 0.144) 12Example 40 Comparative 4.20 5.06 (0.138, 0.142) 18 Example 41Comparative 4.31 5.10 (0.138, 0.142) 12 Example 42 Comparative 4.35 4.91(0.139, 0.143) 15 Example 43 Comparative 5.02 3.98 (0.138, 0.142) 13Example 44 Comparative 4.86 5.00 (0.138, 0.141) 16 Example 45Comparative 4.55 5.21 (0.138, 0.142) 21 Example 46 Comparative 4.80 5.05(0.138, 0.144) 18 Example 47 Comparative 4.21 5.16 (0.138, 0.142) 17Example 48 Comparative 4.57 5.30 (0.138, 0.142) 19 Example 49Comparative 4.48 5.11 (0.138, 0.142) 14 Example 50 Comparative 4.68 5.02(0.138, 0.142) 15 Example 51 Comparative 4.33 5.17 (0.138, 0.142) 21Example 52

As seen in Table 1, it can be confirmed that the organic light emittingdiode using the compound represented by Chemical Formula 1 as theelectron transport material according to the exemplary embodiment of thepresent specification has high efficiency, a low driving voltage, and along life-span as compared to the case where an existing electrontransport material is used.

This is because the compound represented by Chemical Formula 1 is abipolar type including both a p type and an n type, so that hole leakagecan be prevented and an exciton can be effectively confined in the lightemitting layer.

The invention claimed is:
 1. An organic light emitting diode comprising:an anode; a cathode; a light emitting layer provided between the anodeand the cathode; an organic material layer including a compoundrepresented by the following Chemical Formula 1 and provided between thecathode and the light emitting layer; and an organic material layerincluding a compound represented by the following Chemical Formula 2 andprovided between the anode and the light emitting layer,

wherein in Chemical Formula 1, X1 to X3 are the same as or differentfrom each other, and are each independently N or CH, at least one of X1to X3 is N, Cy1 and Cy2 are the same as or different from each other,and are each independently a benzene cycle; or a naphthalene cycle, atleast one of Cy1 and Cy2 is benzene cycle, L1 is a phenylene group; abiphenylene group; or a terphenylene group, m is 1, Ar1 and Ar2 are thesame as or different from each other, and are each independently aphenyl group; a phenyl group substituted by an alkyl group; a biphenylgroup; or a naphthyl group, and

in Chemical Formula 2, Ar3 and Ar4 are the same as or different fromeach other, and are a phenyl group; or a biphenyl group, L2 is aphenylene group; or a biphenylene group, n is an integer of 0 or 1, R1to R7 are each independently hydrogen, and Y1 and Y2 are the same as ordifferent from each other, and are each independently alkyl group,wherein the organic material layer including the compound represented byChemical Formula 1 is an electron transport layer, an electron injectionlayer, or a layer simultaneously transporting and injecting electrons,and wherein the organic material layer including the compoundrepresented by Chemical Formula 2 is a hole transport layer.
 2. Theorganic light emitting diode of claim 1, further comprising: one or twoor more layers selected from the group consisting of an electroninjection layer and an electron transport layer between the lightemitting layer and the cathode.
 3. The organic light emitting diode ofclaim 1, further comprising: one or two or more layers selected from thegroup consisting of a hole transport layer, a hole injection layer, andan electron blocking layer between the light emitting layer and theanode.
 4. The organic light emitting diode of claim 1, wherein thecompound represented by Chemical Formula 1 is a compound represented byany one of the following Chemical Formulas 1-1 to 1-4:

in Chemical Formulas 1-1 to 1-4, X1 to X3, L1, m, Ar1, and Ar2 are thesame as those defined in Chemical Formula 1, Z1 is deuterium, p′ is 0,and p is
 0. 5. The organic light emitting diode of claim 1, wherein X1to X3 are N.
 6. The organic light emitting diode of claim 1, wherein thecompound represented by Chemical Formula 1 is represented by any one ofthe following compounds:


7. The organic light emitting diode of claim 1, wherein hole mobility ofthe compound represented by Chemical Formula 2 is 5×10⁻⁶ cm²/Vs or more.8. The organic light emitting diode of claim 1, wherein Ar3 and Ar4 arethe same as or different from each other, and are each independently asubstituted or unsubstituted phenyl group; a substituted orunsubstituted biphenyl group; or a substituted or unsubstitutedfluorenyl group.
 9. The organic light emitting diode of claim 1, whereinL2 is a substituted or unsubstituted phenylene group; a substituted orunsubstituted biphenylene group; or a substituted or unsubstitutednaphthalene group, or n is
 0. 10. The organic light emitting diode ofclaim 1, wherein Y1 and Y2 are the same as or different from each other,and are each independently a substituted or unsubstituted alkyl grouphaving 1 to 10 carbon atoms; or a substituted or unsubstituted phenylgroup, or are bonded to each other to form a substituted orunsubstituted fluorene structure.
 11. The organic light emitting diodeof claim 1, wherein the compound represented by Chemical Formula 2 isrepresented by any one of the following compounds: